77327-05-0

Basic information

• Product Name: Didemnin B
• Synonyms: Didemnin B;N-(L-Lac-L-Pro-N-Methyl-D-Leu-)cyclo[L-Thr*-[(3S,4R)-3-hydroxy-4-[(S)-1-methylpropyl]-γAbu-]-[(2S,4S)-4-hydroxy*-2,5-dimethyl-3-oxohexanoyl]-L-Leu-L-Pro-N,O-dimethyl-L-Tyr-]
• CAS NO: 77327-05-0
• Molecular Formula: C₅₇H₈₉N₇O₁₅
• Molecular Weight: 1112.36
• Mol File: 77327-05-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 821.94°C (rough estimate)
• Flash Point: 724.5°C
• Appearance: /
• Density: 1.0596 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.6910 (estimate)
• CAS DataBase Reference: Didemnin B(CAS DataBase Reference)
• NIST Chemistry Reference: Didemnin B(77327-05-0)
• EPA Substance Registry System: Didemnin B(77327-05-0)

Safety Data

• Hazardous Substances Data: 77327-05-0(Hazardous Substances Data)

Usage

Description

Didemnin B is a natural product that is predominantly found in the marine organisms Lyngbya majuscula and Trididemnum solidum. It is known for its potent bioactive properties and has garnered significant interest in the field of pharmaceutical research.

Uses

Used in Anticancer Applications:
Didemnin B is utilized as an anticancer agent, particularly effective against various types of cancer. It has demonstrated the ability to inhibit tumor growth and proliferation by targeting specific cellular pathways and processes, making it a promising candidate for cancer treatment.
Used in Drug Delivery Systems:
To enhance the therapeutic potential and bioavailability of Didemnin B, researchers have developed innovative drug delivery systems. These systems, which may include organic and metallic nanoparticles, aim to improve the delivery and efficacy of Didemnin B, ultimately leading to better treatment outcomes for patients with cancer.

InChI:InChI=1/C57H89N7O15/c1-15-33(8)46-44(66)29-45(67)79-49(32(6)7)48(68)34(9)50(69)58-39(26-30(2)3)54(73)64-25-17-19-41(64)56(75)62(13)43(28-37-20-22-38(77-14)23-21-37)57(76)78-36(11)47(52(71)59-46)60-51(70)42(27-31(4)5)61(12)55(74)40-18-16-24-63(40)53(72)35(10)65/h20-23,30-36,39-44,46-47,49,65-66H,15-19,24-29H2,1-14H3,(H,58,69)(H,59,71)(H,60,70)/t33-,34-,35-,36+,39-,40-,41?,42+,43-,44-,46+,47-,49-/m0/s1

Upstream product

• 120286-08-0 Z-didemnin B 
• 129919-85-3 2-<(tert-butyldimethylsilyl)oxy>-L-lactyl-L-proline methyl ester 
• 129919-86-4 2-<(tert-butyldimethylsilyl)oxy>-lactyl-L-proline 
• 129919-87-5 N-methyl-D-leucine 2-(trimethylsilyl)ethyl ester 
• 110720-12-2 N-Z-didemnin A 
• 130008-93-4 cyclo--5-methylheptanoyl>oxy-3-oxo-2,5-dimethylhexanoyl>-L-leucyl>-L-prolyl-N,O-dimethyl-L-tyrosyl>-L-threonyl> hydrochloride 
• 65635-85-0 N-methyl-N-(benzyloxycarbonyl)-D-leucine 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 185461-50-1 cyclo-[N(Me)-O(Me)-Tyr-O-[Boc-(R)-N(Me)-Leu->-Thr-Ist(TBDMS)-Hip-Leu-Pro-> 
• 110825-32-6 Bzl-(S)-Lac-(S)-Pro-OMe 
• 118171-92-9 Bzl-(S)-Lac-(S)-Pro-OH 
• 77327-04-9 Didemnin A 
• 110720-14-4 O-benzyldidemnin B 
• 117710-19-7 L-lactyl-L-prolyl-N-methyl-D-leucine 

Relevant articles and documents

Bacterial biosynthesis and maturation of the didemnin anti-cancer agents

The anti-neoplastic agent didemnin B from the Caribbean tunicate Trididemnum solidum was the first marine drug to be clinically tested in humans. Because of its limited supply and its complex cyclic depsipeptide structure, considerable challenges were encountered during didemnin B's development that continue to limit aplidine (dehydrodidemnin B), which is currently being evaluated in numerous clinical trials. Herein we show that the didemnins are bacterial products produced by the marine α-proteobacteria Tistrella mobilis and Tistrella bauzanensis via a unique post-assembly line maturation process. Complete genome sequence analysis of the 6,513,401 bp T. mobilis strain KA081020-065 with its five circular replicons revealed the putative didemnin biosynthetic gene cluster (did) on the 1,126,962 bp megaplasmid pTM3. The did locus encodes a 13-module hybrid non-ribosomal peptide synthetase-polyketide synthase enzyme complex organized in a collinear arrangement for the synthesis of the fatty acylglutamine ester derivatives didemnins X and Y rather than didemnin B as first anticipated. Imaging mass spectrometry of T. mobilis bacterial colonies captured the time-dependent extracellular conversion of the didemnin X and Y precursors to didemnin B, in support of an unusual post-synthetase activation mechanism. Significantly, the discovery of the didemnin biosynthetic gene cluster may provide a long-term solution to the supply problem that presently hinders this group of marine natural products and pave the way for the genetic engineering of new didemnin congeners.

Total synthesis and structural investigations of didemnins A, B, and C

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Total synthesis of the didemnins. 2. Synthesis of didemnin A, B, C and prolyldidemnin A

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